Time perception is an integral part of daily life experience. However, people often have difficulty in estimating how long an experience lasts (Sackett, Meyvis, Nelson, Converse & Sackett, 2010). Numerous factors can influence duration estimates (Ornstein, 1969; Vroon, 1970; Ahn, Liu & Soman, 2009). In the present research, we investigated whether individuals’ estimates of a task’s duration depend on whether they monitor their progress retrospectively (in terms of the amount of work they have completed) or prospectively (in terms of the amount remaining). Across four studies, we found that when people are asked to estimate the duration of a task shortly before completing it or immediately afterwards, they make shorter estimates when they have monitored their progress prospectively than when they have monitored it retrospectively. When they estimate the task’s duration shortly after beginning it, however, they make longer estimates of its duration in the former case. We attempt to explain why this is the case.